Curing catalyst, resin composition, resin-sealed semiconductor device and coating material

Abstract

A curing catalyst comprising at least one of a cationic curing catalyst component and an organo-metallic compound component. At least one of these components is capable of reversibly repeating the dissolution and precipitation through heating and cooling. The cationic curing catalyst component includes in its molecule at least one substituted or unsubstituted hydrocarbon group having 10 or more carbon atoms, or at least one cyclic organic structure having a substituted or unsubstituted hydrocarbon group having 10 or more carbon atoms.

What is claimed is:  
     
       1. A curing catalyst comprising: 
       an organometallic compound component capable of reversibly dissolving and precipitating through heating and cooling, and selected from the group consisting of the following formulas (II-1), (II-2) and (II-3); and  
       at least one compound selected from the group consisting of organosilane having an aryl group bonded directly to a silicon atom and having a hydroxyl group or a hydrolyzable group bonded directly to a silicon atom, organosiloxane having a hydroxyl group bonded directly to a silicon atom, a phenol compound, an organosilicon compound having a hydrolyzable group bonded directly to a silicon atom, and a silicon compound capable of generating silanol upon irradiation of light,                    
       wherein R 21 , R 22 , R 23  and R 24  may be the same or different and are individually hydrogen atom, substituted or unsubstituted hydrocarbon groups having 1 to 30 carbon atoms with a proviso that one ligand thereof contains at least one substituted or unsubstituted linear or branched alkyl group having 10 or more carbon atoms, which is represented by R 21 , R  22 , R 23  and R 24 ; M is Al; and n is 3. 
     
     
       2. The curing catalyst according to  claim 1 , wherein said compound represented by the formulas (II-1), (II-2) and (II-3) is selected from the group consisting of tris(octadecylacetoacetate) aluminum, tris(hexadecylacetoacetate) aluminum, tris(tetradecylacetoacetate) aluminum, tris(dodecylacetoacetate) aluminum, tris(octylsalicylaidehyde) aluminum, tris(3-octadecylacetylacetate) aluminum, and compounds represented by the following chemical formulas:                  
                 
                   
     
     
       3. The curing catalyst according to  claim 1 , wherein said organosilane having a hydroxyl group bonded directly to a silicon atom is a compound represented by the following formula (S-1):                    
       wherein R 1  is hydroxyl or hydrolyzable group; X 1 , X 2  and X 3  may be the same or different and are individually alkyl group having 1 to 12 carbon atoms; aryl group, phenyl group, tolyl group, paramethoxyphenyl group, parachlorophenyl group and paranitrophenyl group; aralkyl group, benzyl group, phenethyl group, paramethoxybenzyl group and paramethylbenxyl group; alkenyl group, vinyl group, allyl group, propenyl group and butenyl group; and acyl group, acetyl group, benzoyl group and trifluoroacetyl group; and p, q and r are integers of 0 to 3 with a proviso that p+q+r is not more than 3.  
     
     
       4. The curing catalyst according to  claim 1 , wherein said organosiloxane having a hydroxyl group bonded directly to a silicon atom is selected from the group consisting of the following formulas (S-2), (S-3), (S-4) and (S-5);                    
       wherein Y 1 , Y 2 , Y 3 , Y 4 , Y 5  and Y 6  may be the same or different and are individually hydroxyl group or hydrolyzable group; alkyl group having 1 to 12 carbon atoms; aryl group, phenyl group, tolyl group, paramethoxyphenyl group, parachlorophenyl group and paracyanophenyl group; aralkyl group, benzyl group, phenethyl group, paramethoxybenzyl group and paramethylbenzyl group; alkenyl group, vinyl group, allyl group, propenyl group and butenyl group; and acyl group, acetyl group, benzoyl group and trifluoroacetyl group.  
     
     
       5. The curing catalyst according to  claim 1 , wherein said phenol compound is represented by the following general formulas (Ph-1); 
       
         
           Ar 2 —(OH) n   (Ph-1)  
         
       
       wherein Ar 2  is substituted or unsubstituted aromatic or heteroaromatic group; and n is an integer of 1 to 10.  
     
     
       6. The curing catalyst according to  claim 1 , wherein said organosilicon compound having a hydrolyzable group bonded directly to a silicon atom is a compound having alkoxyl group having 1 to 5 carbon atoms; aryloxy group; acyloxy group; alkenyloxy group having 2 to 12 carbon atoms; aralkyloxy group; or a group represented by the following formula:                    
       wherein R′ and R″ may be the same or different and are individually alkyl groups having 1 to 5 carbon atoms.  
     
     
       7. The curing catalyst. according to  claim 1 , wherein said silicon compound capable of generating silanol upon irradiation of light is a compound having any one of groups selected from the group consisting of peroxysilano group, o-nitrobenzyloxy group and α-ketosilyl group. 
     
     
       8. A resin composition, comprising: 
       a curing catalyst and an epoxy resin;  
       wherein said curing catalyst comprises:  
       an organometallic compound component capable of reversibly dissolving and precipitating through heating and cooling and selected from the group consisting of the following formulas (II-1), (II-2) and (II-3), and  
       at least one compound selected from the group consisting of organosilane having an aryl group bonded directly to a silicon atom and having a hydroxyl group or a hydrolyzable group bonded directly to a silicon atom, organosiloxane having a hydroxyl group bonded directly to a silicon atom, a phenol compound, an organosilicon compound having a hydrolyzable group bonded directly to a silicon atom, and a silicon compound capable of generating silanol upon irradiation of light,                    
       wherein R 21 , R 22 , R 23  and R 24  may be the same or different and are individually hydrogen atom, substituted or unsubstituted hydrocarbon groups having 1 to 30 carbon atoms with a proviso that one ligand thereof contains at least one substituted or unsubstituted linear or branched alkyl group having 10 or more carbon atoms, which is represented by R 21 , R 22 , R 23  and R 24 ; M is Al; and n is 3.  
     
     
       9. The resin composition according to  claim 8 , wherein said compound represented by formulas (II-1), (II-2) and (II-3) is selected from the group consisting of tris(octadecylacetoacetate) aluminum, tris(hexadecylacetoacetate) aluminum, tris(tetradecylacetoacetate) aluminum, tris(dodecylacetoacetate) aluminum, tris(octylsalicylaldehyde) aluminum, tris(3-octadecylacetylacetate) aluminum, and compounds represented by the following chemical formulas:                  
                   
     
     
       10. The resin composition according to  claim 8 , wherein said organosilane having a hydroxyl group bonded directly to a silicon atom is a compound represented by the following formula (S-1);                    
       wherein R 1  is hydroxyl or hydrolyzable group; X 1 , X 2  and X 3  may be the same or different and are individually alkyl group having 1 to 12 carbon atoms; aryl group, phenyl group, tolyl group, paramethoxyphenyl group, parachlorophenyl group and paranitrophenyl group; aralkyl group, benzyl group, phenethyl group, paramethoxybenzyl group and paramethylbenzyl group; alkenyl group, vinyl group, allyl group, propenyl group and butenyl group; and acyl group, acetyl group, benzoyl group and trifluoroacetyl group; and p, q and r are integers of 0 to 3 with a proviso that p+q+r is not more than 3.  
     
     
       11. The resin composition according to  claim 8 , wherein organosiloxane having a hydroxyl group bonded directly to a silicon atom is selected from the group consisting of the following formulas (S-2), (S-3), (S-4) and (S-5):                    
       wherein Y 1 , Y 2 , Y 3 , Y 4 , Y 5  and Y 6  may be the same or different and are individually hydroxyl group or hydrolyzable group; alkyl group having 1 to 12 carbon atoms; aryl group, phenyl group, tolyl group, paramethoxyphenyl group, parachlorophenyl group and paracyanophenyl group; aralkyl group, benzyl group, phenethyl group, paramethoxybenzyl group and paramethylbenzyl group; alkenyl group, vinyl group, allyl group, propenyl group and butenyl group; and acyl group, acetyl group, benzoyl group and trifluoroacetyl group.  
     
     
       12. The resin composition according to  claim 8 , wherein said phenol compound is represented by the following formula (Ph-1); 
       
         
           Ar 2 —OH n   (Ph-1)  
         
       
       wherein Ar 2  is substituted or unsubstituted aromatic or heteroaromatic group; and n is an integer of 1 to 10.  
     
     
       13. The resin composition according to  claim 8 , wherein said organosilicon compound having a hydrolyzable group bonded directly to a silicon atom is a compound having alkoxyl group having 1 to 5 carbon atoms; aryloxy group; acyloxy group; alkenyloxy group having 2 to 12 carbon atoms; aralkyloxy group; or a group represented by the following formula:                    
       wherein R′ and R″ may be the same or different and are individually alkyl groups having 1 to 5 carbon atoms.  
     
     
       14. The resin composition according to  claim 8 , wherein said silicon compound capable of generating silanol upon irradiation of light is a compound having any one of groups selected from the group consisting of peroxysilano group, o-nitrobenzyloxy group and α-ketosilyl group. 
     
     
       15. The resin composition according to  claim 8 , further comprising a curing agent. 
     
     
       16. The resin composition according to  claim 15 , wherein said curing agent is selected from the group consisting of acid anhydrides, phenols, aromatic amine compounds, and cyanate ester compounds.